CA1055031A - Process for the preparation of vincamine and other indole alkaloids - Google Patents
Process for the preparation of vincamine and other indole alkaloidsInfo
- Publication number
- CA1055031A CA1055031A CA232,439A CA232439A CA1055031A CA 1055031 A CA1055031 A CA 1055031A CA 232439 A CA232439 A CA 232439A CA 1055031 A CA1055031 A CA 1055031A
- Authority
- CA
- Canada
- Prior art keywords
- vincamine
- reaction
- mls
- starting
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 title claims abstract description 45
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229960002726 vincamine Drugs 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229930005303 indole alkaloid Natural products 0.000 title claims abstract description 6
- 150000002475 indoles Chemical class 0.000 title claims abstract description 5
- GIGFIWJRTMBSRP-ACRUOGEOSA-N (-)-vincadifformine Chemical compound C1C(C(=O)OC)=C2NC3=CC=CC=C3[C@@]22CCN3CCC[C@]1(CC)[C@@H]23 GIGFIWJRTMBSRP-ACRUOGEOSA-N 0.000 claims abstract description 30
- GIGFIWJRTMBSRP-UHFFFAOYSA-N DL-Vincadifformin Natural products C1C(C(=O)OC)=C2NC3=CC=CC=C3C22CCN3CCCC1(CC)C23 GIGFIWJRTMBSRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- NAMSIRMSFVGAKD-UHFFFAOYSA-N vincadifformine Natural products CCC12CCCN3CCC4(C13)C(Nc1cc(OC)ccc41)=C(C2)C(=O)OC NAMSIRMSFVGAKD-UHFFFAOYSA-N 0.000 claims abstract description 14
- JSLDLCGKZDUQSH-RTBUJCADSA-N 19-epivindolinine Natural products O=C(OC)[C@H]1[C@@]23[C@H](C)[C@]4([C@@H]5N(CC=C4)CC[C@]25c2c(N3)cccc2)C1 JSLDLCGKZDUQSH-RTBUJCADSA-N 0.000 claims abstract description 13
- KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 claims abstract description 13
- FNGGIPWAZSFKCN-ACRUOGEOSA-N tabersonine Chemical compound N1C2=CC=CC=C2[C@]2([C@H]34)C1=C(C(=O)OC)C[C@]3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-ACRUOGEOSA-N 0.000 claims abstract description 13
- FNGGIPWAZSFKCN-UHFFFAOYSA-N xi-tabersonine Natural products N1C2=CC=CC=C2C2(C34)C1=C(C(=O)OC)CC3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229930013930 alkaloid Natural products 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 150000003797 alkaloid derivatives Chemical class 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 1
- 229960003903 oxygen Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- RXPRRQLKFXBCSJ-HLAWJBBLSA-N 16-epivincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-HLAWJBBLSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 241001246889 Voacanga Species 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006257 total synthesis reaction Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 229910017974 NH40H Inorganic materials 0.000 description 2
- 240000004627 Voacanga thouarsii Species 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000017105 transposition Effects 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001295727 Amsonia tabernaemontana Species 0.000 description 1
- OZDNDGXASTWERN-CTNGQTDRSA-N Apovincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-CTNGQTDRSA-N 0.000 description 1
- 241000254273 Crioceras Species 0.000 description 1
- 229910015400 FeC13 Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- 241000915727 Rhazya stricta Species 0.000 description 1
- 241001089218 Schizozygia coffaeoides Species 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 241000511964 Tabernaemontana Species 0.000 description 1
- 241000863480 Vinca Species 0.000 description 1
- 241000863486 Vinca minor Species 0.000 description 1
- 235000015799 Voacanga thouarsii Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 description 1
- 229950006936 apovincamine Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003571 thiolactams Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1094074A CH625239A5 (enrdf_load_html_response) | 1974-08-09 | 1974-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055031A true CA1055031A (en) | 1979-05-22 |
Family
ID=4368425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,439A Expired CA1055031A (en) | 1974-08-09 | 1975-07-29 | Process for the preparation of vincamine and other indole alkaloids |
Country Status (28)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358412A1 (fr) * | 1976-07-13 | 1978-02-10 | Parcor | Procede de preparation de la vincamine et d'alcaloides apparentes |
| DE2745415C2 (de) * | 1977-10-08 | 1983-06-23 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur Herstellung von (-)-Vincamin |
| US4285949A (en) * | 1978-12-11 | 1981-08-25 | Omnichem Societe Anonyme | Vincamine derivatives, their preparation and therapeutical use |
| CH646166A5 (it) * | 1980-09-30 | 1984-11-15 | Linnea Sa | Procedimento di sintesi parziale della vincamina e di alcaloidi indolici correlati. |
| CH657617A5 (it) * | 1982-10-25 | 1986-09-15 | Istituto Chemioterapico Di Lod | Procedimento per la preparazione di vincamina. |
| CN102875547B (zh) * | 2011-07-15 | 2015-05-27 | 海南灵康制药有限公司 | 一种长春西汀化合物及其制法 |
| CN102911171B (zh) * | 2012-10-15 | 2015-03-04 | 绍兴民生医药有限公司 | 一种长春西汀的半合成方法 |
| CN103333166B (zh) * | 2013-06-26 | 2016-07-06 | 上海交通大学 | 利用固体酸碱催化合成长春西汀的方法 |
| CN116478161B (zh) * | 2023-04-13 | 2024-09-17 | 海南师范大学 | 一种新的单萜吲哚生物碱类化合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454583A (en) * | 1965-07-19 | 1969-07-08 | Us Health Education & Welfare | Synthesis of vincamine |
| US3770724A (en) * | 1970-03-31 | 1973-11-06 | Roussel Uclaf | Process for preparing pentacyclic alkaloids |
| FR2179620B1 (enrdf_load_html_response) * | 1972-04-14 | 1975-12-26 | Roussel Uclaf | |
| FR2211004A5 (enrdf_load_html_response) * | 1972-12-15 | 1974-07-12 | Synthelabo |
-
1974
- 1974-08-09 CH CH1094074A patent/CH625239A5/it not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR259926A patent/AR207475A1/es active
- 1975-07-22 GB GB30701/75A patent/GB1514337A/en not_active Expired
- 1975-07-23 ZA ZA00754757A patent/ZA754757B/xx unknown
- 1975-07-24 AT AT571375A patent/AT353985B/de active
- 1975-07-25 IN IN1466/CAL/75A patent/IN142318B/en unknown
- 1975-07-29 CA CA232,439A patent/CA1055031A/en not_active Expired
- 1975-07-30 NO NO752683A patent/NO752683L/no unknown
- 1975-07-31 NL NL7509118A patent/NL7509118A/xx not_active Application Discontinuation
- 1975-08-01 ZM ZM112/75A patent/ZM11275A1/xx unknown
- 1975-08-02 BG BG030715A patent/BG24541A3/xx unknown
- 1975-08-05 JP JP50094806A patent/JPS5141399A/ja active Pending
- 1975-08-05 YU YU02013/75A patent/YU201375A/xx unknown
- 1975-08-05 DE DE19752534858 patent/DE2534858A1/de not_active Withdrawn
- 1975-08-06 US US05/602,520 patent/US3979395A/en not_active Expired - Lifetime
- 1975-08-06 BE BE158964A patent/BE832157A/xx not_active IP Right Cessation
- 1975-08-06 RO RO7583094A patent/RO77292A/ro unknown
- 1975-08-07 LU LU73172A patent/LU73172A1/xx unknown
- 1975-08-07 DD DD187741A patent/DD120441A1/xx unknown
- 1975-08-07 SE SE7508896A patent/SE421315B/xx unknown
- 1975-08-07 FR FR7524708A patent/FR2281371A1/fr active Granted
- 1975-08-08 CS CS755512A patent/CS205003B2/cs unknown
- 1975-08-08 PL PL1975182637A patent/PL99452B1/pl unknown
- 1975-08-08 ES ES440120A patent/ES440120A1/es not_active Expired
- 1975-08-08 DK DK360475AA patent/DK141248B/da unknown
- 1975-08-08 SU SU752163172A patent/SU612632A3/ru active
- 1975-08-09 EG EG479/75A patent/EG12908A/xx active
- 1975-08-09 OA OA55582A patent/OA05082A/xx unknown
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